Process of combating fungi with a pinonic acid derivative and a composition of a cellulose ester and said derivative



The methyl ester of pinonic acid (and the Reformatsky derivatives thereof) may also be prepared from crude sulfate turpentine as a starting material, as is more fully set forth in my copending application Serial No. 185,139,

tember 15, 1950. Crude sulfate turpentine is the by-product obtained by the condensation of the releases gases of the pulp digester used in the sulfate pulp process, a process Well known to the art under various names, e. g. the Kraft process, and described e. g., in Rogers Industrial Chemistry, vol. 2, page 1418, 1942. Crude sulfate turpentine contains approximately 70% alpha and 30% beta pinene, together with a-small but disagreeably smelling methyl and other mercaptans and similar sulfur compounds. above-identified copending application Serial No. 185,139, crude sulfate turpentine is converted, in accordance with my invention, by first reacting it with an oxidizing agent, then removing a preponderant proportion of the sulfur compounds (which at that stage separate easily), and finally acidifying, extracting and fractionatingthe residue. The crude pinonic acid (or rather mixture of isomeric pinonic acids) resultin from this process is characterized by a positive test for sulfur; however, these sulfur impurities still remaining, are now present in oxidized form, odorless and otherwise harmless.

In addition to the usefulness of the pinonic acid derivatives as disclosed herein, as plasticizers for cellulose esters and resins of the type obtained by the polymerization of a monomer containing a polymerizable CI-Iz:CI-I- group (such as for instance polystyrene or polyvinyl butyral), they can also serve as plasticizers for natural and synthetic rubbers, as pour point depressants for low temperature lubricants, brake fluids, and leather greases. Their desirable fungistatic properties can be utilized in adhesive compositions, as fixatives in soaps and lotions, as pigment carriers in paints, in protective coatings and lacquers, and other applications.

It will be understood that the various examples given herein are illustrative of specific instances of the production and utilization of terpene carboxylic acid esters in accordance with the present invention, and are not intended to limit the scope of my invention to the particular details set forth in such examples. Inasmuch as variations and modifications within the spirit of my invention will be readily apparent to the expert,

. I intend to encompass such variations and modifications within the scope of my a pended claims.

I claim:

1. A process of combating fungi, comprising applying to the area of expected fungus growth as a fungus resisting compound an ester having the structural formula CH: H omooopm-c-o e;

E2 H our" As stated in my Terpene Carboxylic Acid Esters, filed Sepwherein A is a member of the group consisting of -CO.CH3 and --CZCH.C O 0 02115 2. A process of combating fungi comprising applying as a fungus resisting compound a lower alkyl diester of l-methyl homodehydroethylene pinic acid to the area of expected fungus growth.

3. A process of combating fungi comprising applying as a fungus resisting compound the methyl ethyl diester of l-methyl homodehydroethylene pinic acid to the area of expected fungus growth.

4. A process of combating fungi comprising applying as a fungus resisting compound the methyl ester of pinonic acid to the area of ex- ,pected fungus growth. ,1.a-5:-A*"fungus-resistingcomposition-pf--matter comprising a lower alkanoyl cellulose ester, and as a plasticizer and fungistatic agent therefor an ester having a structural formula Hz H CE;

wherein A is a member of the group consisting of -CO.CH3 and References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 881,827 Rouxeville Mar. 10, 1908 1,752,693 Ramage Apr. 1, 1930 1,963,955 Cleveland June 26, 1934 2,398,492 Bradshaw et a1. Apr. 16, 1946 2,429,603 Borglin et al Oct. 28, 1947 2,450,706 Zeiss Oct. 5, 1948 OTHER REFERENCES The Chemistry of Insecticides and FungicidesFrear (1948), page 154.

Beilstein, Vierte auflage, 1st supplement-vol. 10, pages 297-8 (1932).

Komppa Am. Acad., Sci. Fennicase A 59 1, 3-23 (1943), Chemical Abstracts 41, pages 425-6.

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X oam H. c. GOODRICH 2,707,248 ELECTROMAGNETIC BEAM-CONVERGENCE SYSTEMS FOR TRI-COLOR KINESCOPES 4 Sheets-Sheet l April 26, 1955 Filed Nov. 26, I952 INVENTOR.

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1. A PROCESS OF COMBATING FUNGI, COMPRISING APPLYING TO THE AREA OF EXPECTED FUNGUS GROWTH AS A FUNGUS RESISTING COMPOUND AN ESTER HAVING THE STRUCTURAL FORMULA
 5. A FUNGUS-RESISTING COMPOSITION OF MATTER COMPRISING A LOWER ALKANOYL CELLULOSE ESTER, AND AS A PLASTICIZER AND FUNGISTATIC AGENT THEREFOR AN ESTER HAVING A STRUCTURAL FORMULA 